Alkoxylate blend surfactants

ABSTRACT

Surfactant compositions that include one or more nonionic surfactants derived from seed oils and having a mixture of at least 8, 10 and 12 carbon atom linear alkyl moieties find use in a number of end use applications as substitutes for petroleum derived surfactants.

FIELD OF THE INVENTION

This invention relates to surfactant compositions comprising blends ofalkoxylated alcohols and their use in detergents, hard surface cleaners,foam flotation agents, and emulsifiers.

BACKGROUND OF THE INVENTION

A recent trend promotes production of ultra-concentrated formulations orsystems that contain little or no water. Such formulations orconcentrates are delivered to an end-use customer who then dilutes theconcentrate with water to produce a final working solution. Those whouse concentrates consider it an eco-friendly approach as it eliminatescosts associated with shipping water and reduces material requirementsfor packaging. The concentrates typically include one or more nonionicsurfactants because they are compatible with all other surfactant types(e.g. anionic, cationic and zwitterionic surfactants). In addition,nonionic surfactants resist precipitation with hard water and offerexcellent oil grease cleaning benefits.

Household and industrial applications that employ ultra-concentratesinclude laundry detergents, hard surface cleaners, automatic dishwasherdetergents, rinse aids, emulsification packages (such asagricultural-emulsifiers), and flotation systems (for applications suchas paper de-inking and ore flotation).

Soap and detergent manufacturers use the term “diluted” to refer both todissolution of solids and reduction of concentration of liquids. Forexample, liquid laundry detergent may be diluted in a tub of water.Similarly, a powdered or block laundry detergent that is dissolved in atub of water also would be referred to as “diluted.”

A common problem for concentrated formulas that contain surfactants isformation of gels when a solid or liquid surfactant is diluted withwater. For example, a formulation or concentrate consisting primarily ofa 9-mole ethoxylate of nonylphenol (such as Tergitol™ NP-9) formsresilient, slow-dissolving gels when mixed with water. For end-usecustomers (especially household customers), these slow-dissolving gelsrequire extensive mixing which can interfere with convenience andeffectiveness of end-use or diluted formulations. One way the industryexpresses a tendency of a surfactant to cause gels is a “gel range.” Atypical gel range describes a percentage of samples that form gels, outof a number of samples, each having increasing surfactant concentration.For example, a gel range of less than 20% indicates that less than twosamples out of nine samples form gels; the nine samples havingsurfactant concentrations of 10 wt. %, 20 wt. %, 30 wt. %, 40 wt. %, 50wt. %, 60 wt. %, 70 wt. %, 80 wt. %, and 90 wt. %, each weightpercentage (wt %) being based upon combined weight of surfactant andde-ionized water. A sample forms a gel when it is non-pourable for atleast five seconds at 23° centigrade (° C.) when its container isinverted 180° so the container's open spout or mouth faces down. Formany applications, a surfactant ideally has no gel range. In otherwords, it does not form gels when mixed with water.

In some cases, the tendency to form gels can be overcome by adding ananti-gelling agent such as a solvent or a polyglycol to the formulation.For example, a simple formulation containing 20 wt % of a 9-moleethoxylate of nonylphenol (Tergitol™ NP-9) and 80 wt % propylene glycol(each wt % based on formulation weight) will not form gels upon dilutionwith water. However, the addition of anti-gelling agents tends toincrease overall complexity and cost of the formulation, and thereforemay be undesirable.

In addition to gel formation tendency, an important physical propertyconsideration for use in selecting a surfactant is its tendency toundergo a viscosity increase as temperatures fall or decrease.Surfactant users typically select “pour point” or “pour pointtemperature” as a general indicator of handling characteristics of apure surfactant under reduced temperatures. They consider pour point asthat temperature below which a liquid surfactant will fail to pour froma container.

Many nonionic surfactants are alkoxylates of fatty alcohols containinggreater than about eight carbons (C₈₊). The alkoxylates are typicallyblock or random polymers of ethoxy, propoxy, butoxy, or even largeralkoxy groups. These alkoxylates vary in alkyl group size, usuallyrepresented by “R”, and in number of alkoxy groups in a polymer chain,also referred to as “degree of alkoxylation”. The number and size ofalkoxylate groups affects surfactant performance attributes includingdispersibility and stability in various solutions, detergency, foamformation, and cleaning performance.

In recent years, the global chemical industry has expressed increasinginterest in using renewable resources, such as plant or seed oils, toreduce dependence on petroleum and natural gas feedstocks. Seed oilscontain fatty acids that may be converted to alcohols using knowntechnology. The alcohols, in turn, may be converted to alcoholalkoxylates by methods such as those discussed in “NonionicSurfactants”, Martin, J. Schick, Editor, 1967, Marcel Dekker, Inc., orUnited States Patent Application Publication (USPAP) 2005/0170991A1.Fatty acid alcohols may also be alkoxylated using metal cyanidecatalysts including (but not limited to) those described in U.S. Pat.No. 6,429,342.

Alcohols derived from natural feedstocks tend to have carbon chains thatare more linear, and less branched, than alcohols derived from petroleumand natural gas products, which may be regarded as semi-linear orbranched. In addition, when produced via hydrogenation of fatty acids,alcohols tend to be primary alcohols, having only one reactive group andan even number of carbon atoms in each chain or molecule. Whenalkoxylated, natural feedstock-derived alcohols produce surfactants thatmay behave somewhat differently than their petroleum and natural gasanalogs. For example, alkoxylates with a generally linear structure tendto self-associate and form gels to a greater extent in water than thosewith a semi-linear or branched structure. As such, surfactants basedupon alkoxylated, natural oil-derived alcohols often do not function asdrop in replacements for surfactants based upon alkoxylated alcoholsderived from petroleum and natural gas feedstocks. As they are not dropin replacements, formulators must accommodate differences betweensurfactants based on natural oils and surfactants based upon petroleumor natural gas in preparing formulations for various uses.

Relatively short-chain alkoxylates of linear alcohols derived frompetroleum or natural gas, i.e. those where R contains from 6 to 10carbon atoms (C₆₋₁₀ or C₆-C₁₀), typically do not form gels, and areoften used in applications to avoid gel formation. For example, Triton™XL-80N, based on an alkoxylate of a C₈-C₁₀ blend of alcohols, exhibits anarrow gel range (less than 20% of the range from 0% to 100% dilution)and is often used in hard-surface formulations that require rapiddissolution in the absence of gels. Other short-chain alkoxylates thathave no gel range include Plurafac™ SLF-62 (based on a C₆₋₁₀ alkoxylateblend), Alfonic™ 810-60 (a C₈-C₁₀ ethoxylate), and Surfonic™ JL-80X (aC₈₋₁₀ alkoxylate)

Although these relatively short-chain alkoxylates of linear alcoholsform few, if any, gels upon dilution with water, they perform poorly insome applications. For example, the C₈-C₁₀alkoxylates of linear alcoholsdo not perform well in some standard laundry cleaning tests. Conversely,formulations with relatively long-chain alkoxylates of linear alcoholsderived from petroleum or natural gas, e.g. C₁₁₋₁₆ alcohol ethoxylates,have better detergent performance than the C₈-C₁₀ alkoxylates of linearalcohols, but tend to form more gels. Gel formation is even more of aproblem for C₁₂₋₁₈ seed-oil based alcohol ethoxylates, since thesematerials are 100% linear and form gels that are very difficult todissolve in water.

One approach to improve general properties such as detergency, oilremoval, or metal cleaning is to use blends of two or more nonionicsurfactants. However, blends of alkoxylates, especially C₁₀₋₁₆ alcoholalkoxylates, to give surfactants with specific properties (e.g. acertain pour point, a low or reduced gel range, and a desireddetergency) when used in an ultra-concentrated formulas appear to beunknown.

U.S. Pat. No. 3,983,078 teaches the use of mixtures of long-chainalkylene oxide surfactants and short-chain alkylene oxideco-surfactants. The mixtures have a hydrophilic-lipophilic balance (HLB)in a range of from about 10.8 to 12.0. These surfactants blends areclaimed as one part of complex formulations or blends that incorporatebuilders (sodium tripolyphosphate), hydrotropes (sodium toluenesulfonate), thickeners (sodium carboxymethyl cellulose), and otheradditives. In this case, “long-chain” refers to a formula:R—O—(C_(y)H_(2y)O)_(a)—(C_(z)H_(2z)O)_(b)—C_(w)H_(2w)OH, where R rangesfrom C₈₋₁₅, a=0-11; b=0-11; a+b=4-11; y=2-3; z=2-3; w=2-3; and “shortchain” encompasses a formula R₁—O—(C₂H₄)_(x)—C₂H₄OH, where R₁=C₈₋₁₁ andx=3.5-5. Illustrative mixtures include 60-80 wt % of the “long chain”component” and 20-40 wt % of the “short-chain” component, the weightpercentages being based upon mixture weight and totaling 100 wt %.

U.S. Pat. No. 4,965,014 describes liquid nonionic surfactant mixtureshaving a general formula R—O—(PO)₁₋₂(EO)₆₋₈(H) where PO refers topropylene oxide, EO refers to ethylene oxide, O represents oxygen and Hrepresents hydrogen. The mixtures have components with R selected sothat C₈=0 to 5%, C₉₋₁₀=75-90%, C₁₁₋₁₂=5-15%, C₁₃₋₁₄=4-10%, C₁₅₋₁₆=0 to3%.

Patent Cooperation Treaty Publication (WO) 94/10278 describes blends ofsurfactants based on a mixture of component A with component B in weightratios ranging from 4:1 to 10:1 (80 wt % to 91 wt % component A).Component A is defined as R¹—(OC₃H₆)n-(OC₂H₄)p-OH, in which R¹ is analkyl residue with 6 to 10 carbon atoms, n is a number from 0.5 to 8, pis a number from 4 to 10. Component B is defined as R²—(OC₂H₄)_(q)—OH,in which R² is an alkyl residue with 10 to 22 carbon atoms and q is anumber from 4 to 10. The example teaches a blend of 85% of a C₈alkoxylate with 15% of a C₁₂₋₁₄ ethoxylate.

SUMMARY OF INVENTION

One aspect of this invention is a surfactant composition comprising atleast one nonionic surfactant represented by Formula (I)

R—O—(C₃H₆O)_(x)(C₂H₄O)_(y)—H  (I)

wherein x is a real number within a range of from 0.5 to 3, y is a realnumber within a range of from 2 to 10, and R is a mixture of seed-oilbased linear alkyl moieties with an alkyl moiety distribution as followswherein each wt % is based upon weight of all alkyl moieties present inthe distribution and all wt % for each distribution total 100 wt %:

Carbon Atoms in Moiety Amount C₆  0 wt %-40 wt % C₈ 20 wt %-40 wt % C₁₀20 wt %-45 wt % C₁₂ 10 wt %-45 wt % C₁₄  0 wt %-40 wt % C₁₆—C₁₈  0 wt%-15 wt %

The surfactant compositions of the present invention preferably combinedetergency or cleaning performance typical of C₁₁-C₁₆ branched orsemi-branched alkyl alkoxylates derived from petroleum with gel rangesand, more preferably, pour points and, still more preferably,dissolution in water characteristics, typical of C₆-C₁₀ branched orsemi-branched alkyl alkoxylates derived from petroleum.

The surfactant compositions of the present invention exhibit at leastone, preferably more than one, and still more preferably all of severalphysical or performance properties. The properties are: a) a gel rangeof less than 20% when mixed with water; b) a pour point of less than 10°C., c) detergency for laundry; d) dynamic surface wetting and textilewetting similar to Tergitol NP-9 Surfactant; e) biodegradability asdefined by European Detergent Directive (OECD 301 test); f) desirablefoam properties based on Ross-Miles Foam test (initial foam >100 mm, 5min foam <50 mm); g) dissolution time in water of less than 2 minutes;h) wetting times of less than 50 seconds at a surfactant in waterconcentration of 0.05 wt %, based on total weight of surfactant andwater and i) a critical micelle concentration less than 500 ppm.

The surfactant compositions of this invention find utility inultra-concentrates, especially those used in applications such aslaundry, hard surface cleaning, emulsification, and foam flotationprocesses. In particular, the surfactant compositions of this inventionmay replace conventional, petroleum-derived nonylphenol ethoxylates,alcohol ethoxylates or alcohol alkoxylates in many applicationsincluding (but not limited to) laundry detergents, hard surface cleaningagents, paints, coatings, flotation processing, emulsification, generalwetting, adjuvants for agricultural chemicals, textile cleaning, textileprocessing, pulp processing, paper processing, mining, polyurethane foamprocessing, personal care, and oil field recovery.

As detailed below, surfactant compositions of this invention comprisealkoxylates having at least three different length alkyl groups, with apreferred subset including at least four different length alkyl groups.The surfactant compositions of this invention have improved detergency,dissolution and handling properties relative to surfactant compositionshaving the same number of carbon atoms in alkyl groups, but derived frompetroleum or natural gas. The surfactant compositions of the presentinvention have particular utility in an ultra-concentrate formulationwhere they constitute from 2 wt % to 90 wt % of the formulation, basedupon total formulation weight. The surfactant compositions of thepresent invention allow one to minimize, preferably eliminate, use ofanti-gelling agents, such as solvents or polyglycols, in formulatingsuch ultra-concentrates.

DESCRIPTION OF THE INVENTION

Each occurrence of a range in this application includes both endpointsthat establish the range unless otherwise stated. In other words, arange of from 2 to 10 necessarily includes both 2 and 10 unlessotherwise stated.

The surfactant compositions of the present invention comprise at leastone, preferably more than one, nonionic surfactant represented byFormula (I)

R—O—(C₃H₆O)(C₂H₄O)_(y)—H  (I)

In Formula (I), each C₃H₆O moiety may also be called apoly(oxypropylene) or PO moiety and each C₂H₄O moiety may also be calleda poly(oxyethylene) or EO moiety. In addition, x is a real number withina range of from 0.5 to 3 and y is a real number within a range of from 2to 10. Finally, R represents a mixture of linear alkyl moieties, mostpreferably a mixture of linear alkyl moieties that are alkoxylates ofseed oil-derived alcohols. Even more preferably, R has an alkyl moietydistribution in accord with ranges shown in Table I below.

TABLE 1 Percentages of alkyl moieties Alkyl Moiety Carbon Chain WeightLength Percent C₆  0-40 C₈ 20-40 C₁₀ 20-45 C₁₂ 10-45 C₁₄  0-40 C₁₆  0-15

As shown in Table 1, R can be a mixture of just three alkyl moieties,C₈, C₁₀ and C₁₂. Any one or more of C₆, C₁₄ and C₁₆ alkyl moieties may,but need not be, present in surfactant compositions of the presentinvention. When present, the amounts of C₆, C₁₄ and C₁₆ alkyl moietiesmay satisfy any of their respective ranges as shown in Table 1 as longas all weight percentages total 100 wt %.

The surfactants of the present invention, sometimes generically referredto as alkoxylates, are preferably prepared in a sequential manner thatincludes propoxylation (adding PO or poly(oxypropylene)) moieties of analcohol or mixture of alcohols to form a PO block followed byethoxylation (adding EO or poly(oxyethylene)) moieties to form an EOblock attached to the PO block, but spaced apart from R which representsalkyl moieties from the alcohol or mixture of alcohols. One may eitherbegin with a mixture of alcohols that provides a distribution of alkylmoieties and then sequentially propoxlylate and ethoxylate the mixtureor separately propoxylate and ethoxylate select alcohols and thencombine such alkoxylates (propoxylated and ethoxylated alcohols) inproportions sufficient to provide a distribution as shown in Table 1above.

Formula (I) above includes variables “x” and “y” that, taken together,establish a degree of alkoxylation in an oligomer distribution.Individually, “x” and “y” represent average degrees of, respectively,propoxylation and ethoxylation. The degree of propoxylation or “x”preferably falls within a range of from 0.5 to less than 4, morepreferably within a range of from 0.5 to 3, still more preferably withina range of from 2 to 3, and even more preferably within a range of from2.5 to 3. The degree of ethoxylation or “y” preferably falls within arange of from 2 to 10, more preferably within a range of from 2 to 8,still more preferably within a range of from 4 to 8 and even morepreferably within a range of from 6 to 8.

As a general rule in selecting degrees of propoxylation andethoxylation, note that as propoxylation of a conventional C₈ surfactantderived from petroleum increases so does detergency of the surfactant,but a tradeoff occurs in that propoxylation or an “x” value in excess ofabout 3 typically leads to a decrease in biodegradability.

A preferred subset of surfactant compositions of the present inventionas represented by Formula (I) include x being within a range of from 2.5to 3, y remaining within a range of from 2 to 10 and R has an alkylmoiety distribution as shown in Table 2 below.

TABLE 2 Percentages of alkyl moieties Alkyl Moiety Carbon Chain WeightLength Percent C₆  0-36 C₈ 22-40 C₁₀ 27-44 C₁₂ 14-35 C₁₄  5-13 C₁₆ 0-5

In other words, the surfactant compositions as shown in Table 2 mustinclude a mixture of at least four alkyl moieties, C₈, C₁₀, C₁₂ and C₁₄.Either or both of C₆, and C₁₆ alkyl moieties may, but need not be,present in surfactant compositions of this preferred subset of thepresent invention. When present, the amounts of C₆ and C₁₆ alkylmoieties may satisfy any of their respective ranges as shown in Table 1as long as all weight percentages total 100 wt %.

The following examples illustrate, but do not limit, the presentinvention. All parts and percentages are based upon weight, unlessotherwise stated. All temperatures are in ° C. Examples (Ex) of thepresent invention are designated by Arabic numerals and ComparativeExamples (Comp Ex) are designated by capital alphabetic letters.

Comp Ex A: Preparation of C₈₋₁₀O(PO)₃(EO)_(5.5)H

Combine equal weights (1000 gram (g) each) of 1-octanol (99%) (AldrichCat 47232-8) (CAS# 111-87-5) and 1-decanol (decyl alcohol) Aldrich Cat#12-058-4 (CAS# 112-30-1) to form an alcohol blend. Add 3 g of flakedpotassium hydroxide (KOH) to 1000 g of the alcohol blend to form acatalyzed mixture. Distill the catalyzed mixture under a partial vacuum(50 millimeters of mercury (mm Hg)) with a nitrogen purge for 45 minutesand a temperature of 100° C., or until catalyzed mixture has a watercontent of less than 500 parts by weight per million parts by weight ofcatalyzed mixture (ppm).

Add 1210 g of propylene oxide (PO) to the distilled, catalyzed mixturewith stiffing to provide a first combined mixture and heat the firstcombined mixture to a temperature of 130° C. With continued stirring,maintain the first combined mixture at a temperature of 130° C. for fourhours to allow propoxylation to proceed substantially to completion andyield a propoxylated intermediate.

With continued stirring and maintenance of the 130° C. temperature, add1685 g of ethylene oxide to the propoxylated intermediate to provide asecond combined mixture. Maintain stirring and the 130° C. temperaturethrough addition of 1685 g of ethylene oxide (EO) and for a period oftwo hours thereafter to allow ethoxylation to proceed substantially tocompletion as evidenced by a residual EO content of less than 10 ppm,based upon weight of the second combined mixture, and yield a rawproduct.

Cool the raw product to a temperature of 70° C. then add neutralize with2.4 g of acetic acid to yield a propoxylated and ethoxylated surfactant.The surfactant has a final cloud point, measured as a 1 wt % aqueoussolution, in accord with American Society for Testing and Materials(ASTM) D2024 of 46.3° C.

Comp Ex B: Preparation of C_(12-C14)O(PO)₂(EO)₇H

Combine equal weights (1000 grams each) of 1-dodecanol (98%) (Aldrich44381-6) (CAS# 112-53-8) with 1-Tetradecanol (Aldrich T-960-5) (CAS #112-72-1) to form a blend of C₁₂ and C₁₄ alcohols. Add 2 g of flaked KOHto 900 g of blend to form a catalyzed mixture as in Ex 1.

Replicate Ex 1 with changes to first propoxylate with 540 g of PO, thenethoxylate with 1540 g of EO and neutralize with 1.5 g of acetic acid.The resulting propoxylated and ethoxylated surfactant has a final cloudpoint of 51° C.

Ex 1: Preparation of C₆₋₁₆ alkoxylate Using Pre-Blended Alcohols

Combine 500 g of a seed-oil derived C₈₋₁₀ alcohol, with a hydroxylnumber of approximately 386 (corresponding to a blend consisting ofabout 55% n-decanol and about 45% n-octanol) with 500 g of a seed-oilderived C₁₂₋₁₆ blend having a hydroxyl value of approximately 288(corresponding to a blend consisting of about 70% n-dodecanol, 25%n-tetradecanol and 5% n-hexadecanol) to provide a mixed alcohol stream.The mixed alcohol stream provides an alkyl moiety weight percentagedistribution as follows: C₈=22.5%, C₁₀=27.5%, C₁₂=35%, C₁₄=12.5 andC₁₆=2.5%.

Add 3 g of flaked KOH to the mixed alcohol stream to form a catalyzedmixture as in Ex 1. Distill 633.57 g of the catalyzed mixture as in Ex1, but reduce time at temperature from 45 minutes to 10 minutes.Replicate Ex 1 with changes to first propoxylate with 540 g of PO, thenethoxylate with 820 g of EO the distilled, catalyzed mixture. Effect rawproduct neutralization with 2.2 g of acetic acid.

The propoxylated and ethoxylated surfactant has a final cloud point of34.4° C. and a structure (based on raw material feeds) ofC₈₋₁₆O(PO)_(2.5)(EO)₅H.

Comp Ex C: C₈₋₁₀O(PO)_(2.5)(EO)_(6.5)H

Replicate Ex 1 with changes to convert 1035 g of a seed-oil derivedC₈₋₁₀ alcohol to a propoxylated and ethoxylated surfactant. The alcoholhas a hydroxyl number of approximately 386 (corresponding to a blendconsisting of about 55% n-decanol and about 45% n-octanol). The changesinclude distillation for 30 minutes at 5 mm Hg rather than 45 minutes at50 mm Hg as in Comp Ex A to attain a water content of less than 200 ppm.The changes also include 1050 g of PO, 1590 g of EO, addition of EObefore propoxylation proceeds to a point where residual or unreacted POreaches a level of less than 50 ppm and an increase in amount of aceticacid to 2.7 g.

The propoxylated and ethoxylated surfactant has a final cloud point of51.2° C. and a structure (based on raw material feeds) ofC₈₋₁₀O(PO)_(2.5)(EO)₆₅H.

Comp Ex D: C₁₂₋₁₄O(PO)_(2.5)(EO)₈H

Replicate Comp Ex C with changes to prepare a propoxylated andethoxylated surfactant from 998 g of a seed-oil derived C₁₂₋₁₆ blendwith a hydroxyl value of approximately 288 (corresponding to a blendconsisting of about 70% n-dodecanol, 25% n-tetradecanol and 5%n-hexadecanol). The changes include reducing distillation time to 15minutes, propoxylation with 750 g of PO, ethoxylation with 1815 g of EOand neutralization with 2.6 g of acetic acid.

The propoxylated and ethoxylated surfactant has a final cloud point of54.5° C. and a structure (based on raw material feeds) ofC₁₂₋₁₄O(PO)_(2.5)(EO)₈H.

Comp Ex E:A 50:50 blend of Comp Ex A (C₈₋₁₀O(PO)₃(EO)_(5.5)H) and CompEx B (C₁₂-C₁₄O(PO)₂(EO)₇H)

Produce a simple mixture of two separately prepared surfactants bymixing 100 g of the surfactant of Comp Ex A with 100 g of the surfactantof Comp Ex B.

Ex 2: A 65:35 blend of Comp Ex C(C₈₋₁₀O(PO)_(2.5)(EO)_(5.8)H) and CompEx D (C₁₂-C₁₄O(PO)_(2.5)(EO)₈H)

Replicate Comp Ex E using 130 g of the surfactant of Comp Ex C and 70 gof the surfactant blend of Comp Ex D. The resulting blend of seed-oilbased surfactants has an R group distribution as follows: C₈=28.09 wt %,C₁(O)=34.34 wt %; C₁₂=26.30 wt %; C₁₄=9.39 wt % and C₁₆=1.88 wt %, eachwt % being based upon total distribution weight.

Example 3 Application Testing

Draves Wetting Test American Association of Textile Chemists andColorists (AATCC) Test 17 (ASTM D2281) Prepare 0.05 wt %, 0.10 wt % and0.15 wt % solutions of surfactant in deionized water. Place a cottonskein (40/2 combed peeler yarn from Testfabrics, Inc.) in each solutionand measure elapsed time until the skein collapses. In addition,calculate a concentration of surfactant required for wetting in 20seconds based on a linear regression of a log time versus logconcentration plot built on data from the 0.05 wt %, 0.10 wt % and 0.15wt % solution testing

Ross-Miles Foam Height Test ASTM D1173

Surface Tension and Critical Micelle Concentration (CMC) MeasurementMeasure surface tension (dyne/centimeter (dyne/cm) using a Wilhelmyplate) of a surfactant-water solution while incrementally addingsurfactant to de-ionized water, and plot test results versus surfactantconcentration. The Critical Micelle Concentration is the point at whichan increase in surfactant concentration no longer results in a changesurface tension.

Pour Point Test—ASTM Test D97

Dissolution Time Test—Measure time required for 50 g of a surfactant todissolve in one liter (L) of water at 20° C. with stirring using anoverhead stirrer operating at a stirring rate of 500 revolutions perminute (rpm).

Subject surfactants from Comp Ex A-E, Ex 1-2, two commercial surfactants(Comp Ex F=TERGITOL™ NP-9, commercially available from The Dow ChemicalCompany; Comp Ex G=NEODOL™ 25-7, commercially available from ShellChemicals) and an experimental surfactant (Comp Ex H) that has the samecomposition as Comp Ex A save for reversing order of propoxylation andethoxylation to Draves Wetting Testing, Surface Tension Testing,Critical Micelle Concentration Testing and Ross Miles Foam HeightTesting (Initial and Final (after five minutes)) and summarize testresults in Table 3 below. For reference purposes, deionized water has asurface tension of 73 dynes/cm. In addition, subject surfactants fromComp Ex A-G and Ex 1-2 to Pour Point Testing, Dissolution Time Testingand Gel Range Testing and summarize test results in Table 4 below where,for Gel Range Testing, L=liquid, G=gel and S=solid.

TABLE 3 Wetting Times, Sec (Draves) 20 Sec Surface Tension Ross WettingSurface Miles Foam Conc. CMC Tension at Initial Final Example 0.05%0.10% 0.15% Wt % (ppm) 0.1 Wt. % (mm) (mm) Ex. 1 29.5 10.5 5 0.06 11 30110 25 Ex. 2 40 11 5.5 0.09 18 29 120 10 Comp. Ex. A 38 7.5 3.5 0.07 19029 109 22 Comp. Ex. B 38 17 10 0.09 11 30 105 20 Comp. Ex. C 48 10 4.50.07 115 29 105 15 Comp. Ex D 36 18 10 0.09 16 31 105 50 Comp. Ex. E 3810 7 0.07 33 29 115 40 Comp. Ex. F 34 12 6 0.07 20 30 148 35 Comp Ex. G63 22 13 0.11 11 28 105 100 Comp. Ex. H 137 10 5 0.09 530 30 60 5

The data in Table 3 demonstrate that order of alkoxylation is important,at least in terms of Draves Wetting Times for a 0.05 wt % concentrationof surfactant, CMC and Ross Miles Foam Height Testing results as shownby comparing Comp Ex A (propoxylation followed by ethoxylation) and CompEx H (ethoxylation followed by propoxylation). The data in Table 3 alsodemonstrate that seed-oil based surfactants of the present inventionperform well in Draves and Ross Miles Foam testing and have a desirableCMC. As shown in Table 4 below, such surfactants also have a low GelRange.

TABLE 4 Pour Dissolution Point, Time Gel Range, Percent Surfactant inWater at 23 C. Example ° C. (Min:sec) 10% 20% 30% 40% 50% 60% 70% 80%90% 100% Ex. 1 −3 0:30 L L L L L L L L L L Ex. 2 6 0:20 L L L L L L L LL L Comp. Ex. A 3.5 0:05 L L L L L L L L L L Comp. Ex. B 14.5 20.00  L LL G G G G G L L Comp. Ex C 6 0:06 L L L L L L L L L L Comp. Ex. D 1620:00  L L L G G G G G L L Comp. Ex. E 4 0:50 L L L L G L L L L L Comp.Ex. F −1 8:32 L L L L L G G G L L Comp Ex. G 26 16:00  L L L G G G G G LS L = Liquid, G = Gel, S = Solid

The data in Table 4 demonstrate that seed-oil based surfactants of thepresent invention with an R group distribution as specified above have acombination of a narrow gel range (less than 20% of the range from 0% to100% dilution), coupled with a rapid dissolution time (less than 2minutes) and a low pour point (less than 10° C.). Surfactants that lacka C₈-C₁₀ fraction, such as Comp Ex B and Comp Ex D tend to have anunacceptably broad gel range, an excessively long dissolution time, andan unacceptably high pour point.

Ex 4: Detergent Performance Properties of Surfactant Blends.

Perform laundry testing using a Terg-O-Meter with test conditions asfollows: agitation rate=100 cycles/minute; wash temperature=40° C.; washbath size=1 L; polyester/cotton swatches 3-in. by 3-in. (7.5-cm.by7.5-cm) square, with pinked edges, using Sebum/Pigment (STC EMPA 119)from Testrabrics™. Wash the fabric swatches, using de-ionized water with300 ppm surfactant. Measure the delta reflectance using a HunterColorimeter in the “reflectance” mode. Summarize test results in Table 5below. In addition to using surfactants from Comp Ex A-E and Ex 1-2, andcommercial surfactants (Comp Ex F and Comp Ex G), Comp Ex I represents acontrol with only deionized water.

TABLE 5 Delta Reflectance Example (Terg-o-meter) Ex 1 6.314 Ex 2 9.386Comp Ex A 1.202 Comp Ex B 10.482 Comp Ex C 3.016 Comp Ex D 11.446 CompEx E 9.336 Comp Ex F 11.988 Comp Ex G 11.496 Comp Ex I 0.734

The data in Table 5 show that certain surfactants perform better thanothers from a laundry detergency point of view. Surfactants based onC8-C10 alcohols (Comp Ex A, Comp. Ex. C) show poor detergent performance(where “poor” is defined as <5 delta reflectance units, as shown inTable 5) but excellent dissolution times, pour points, and gel ranges(as shown in Table 4). Surfactants based on C12+ alcohols (Comp. Ex. F,Comp. Ex. G, Comp. Ex. B, Comp. Ex. D) show good laundry performance(where “good” is defined as >9 delta reflectance units as shown in Table5) but poor dissolution times and gel ranges (as shown in Table 4). Onlythose surfactants based on critical C8-C10 and C12-C14 blends (Comp ExE, a petroleum-based surfactant and Ex. 2, a seed oil-based surfactant)show both moderate to good laundry performance (where moderate to goodis defined as >5 delta reflectance units) and excellent dissolutiontimes, pour points, and gel ranges.

1. A surfactant composition comprising at least one nonionic surfactantrepresented by formula (I)R—O—(C₃H₆O)_(x)(C₂H₄O)_(y)—H  (I) wherein x is a real number within arange of from 0.5 to less than 4, y is a real number within a range offrom 2 to 10, and R is a mixture of seed-oil based linear alkyl moietieswith an alkyl moiety distribution as follows wherein each wt % is basedupon weight of all alkyl moieties present in the distribution and all wt% for each distribution total 100 wt %: Carbon Atoms in Alkyl MoietyAmount C₆  0 wt %-40 wt % C₈ 20 wt %-40 wt % C₁₀ 20 wt %-45 wt % C₁₂ 10wt %-45 wt % C₁₄  0 wt %-40 wt % C₁₆—C₁₈  0 wt %-15 wt %


2. The composition of claim 1 wherein x is a real number less than orequal to
 3. 3. The composition of claim 1, wherein x is a real numberwithin a range of from 2-3.
 4. The composition of claim 1, wherein x isless than y.
 5. The composition of claim 1, wherein y is greater than orequal to 2 times x.
 6. The composition of claim 1, wherein x is from 2.5to 3, and the alkyl moiety is as follows: Carbon Atoms in Alkyl MoietyAmount C₆  0-36% C₈ 22-40% C₁₀ 27-44% C₁₂ 14-35% C₁₄  5-13% C₁₆—C₁₈ 0-5%


7. The composition of claim 1, whereby the composition has a pour pointof less than 15° C.
 8. The composition of claim 1, whereby thecomposition has a critical micelle concentration in de-ionized water ofless than about 200 ppm.
 9. The composition of claim 1, wherein a 0.05wt.
 10. The composition of claim 1, wherein a 0.1% solution of thecomposition in de-ionized water has a surface tension of less than 31dynes/cm.
 11. The composition of claim 1, wherein the composition has agel range of less than 20%.
 12. A detergent or cleaner, comprising thecomposition of claim 1 in an amount within a range of from 1 weightpercent to 99.1 weight percent, in each case based on total weight ofthe detergent or cleaner.
 13. The detergent or cleaner of claim 12,further comprising an additive and de-ionized water.